Leading Through Change: John Caplan

Leigh Buchanan is an editor-at-large for Inc. magazine. A former editor at Harvard Business Review and founding editor of Webmaster Magazine, she writes regular columns on leadership and workplace culture.

It's rare to hear of a career that sounds as sparkly as that of John Caplan. Speaking at the Inc. Leadership Forum in Miami, the founder and CEO of OpenSky, a personalized shopping site curated by celebrities, described lofting Serena Williams's Wimbledon Trophy over his head during a visit to her home and trying on Shaquille O'Neal's sneakers while signing him up for the service. Before launching OpenSky--which also works with stars such as Martha Stewart and Bobby Flay pointing customers toward their favorite things--Caplan was the first non-Ford-family CEO of Ford Models, a troubled business blessed with hot-and-cold-running beauty.

But to get there, Caplan traveled a long road cobbled with lessons learned, which he shared with the Inc. audience.

After his initial success at a company that sold ads on billboards and on busses--a job Caplan cheerfully admits he obtained through nepotism--he started his own ad company. For one key customer, Arizona Iced Tea, he created big, beautiful packages that held 24 ounces but sold for a 16-ounce price. On Friday nights he and his colleagues drove around town in a limo tearing down Snapple signs and replacing them with Arizona Iced Tea posters.

After failing at a cigar-of-the-month club venture, which never attracted the millions of aficionados he had hoped for, Caplan went back to work for someone else: this time an ad agency where he worked on the Starbucks campaign and absorbed this bit of wisdom from his employers: "Put your radar up. The best entrepreneurs are good listeners."

Caplan moved from there to Mining.com, soon re-branded About.com, where he used search engine marketing to create the fifth most popular advertising site on the Internet. His lesson from that experience involved consensus: Don't attempt it.

"Consensus is the worst thing that can happen to a company," said Caplan. With consensus great decisions get watered down. Teamwork is the better approach: "but the kind of teamwork where we kill together, not where we're best friends," he said. "Goal-aligned teams kick ass."

He joined Ford Models when it was losing money and cachet and turned it around by creating packages of talent for clients, empowering business units to be entrepreneurial, and launching a media business. Then he sold it, "the only way to make real money," he told the audience.

At 40, Caplan started OpenSky, raising $5 million in six weeks. But his first model--giving bloggers a way to build stores within their blogs failed. "Consumers reading blogs don't have credit cards in their hands," he explained. He almost gave up but instead started over: "the most exhilarating and brutal experience I've ever had," he said. "I had to break up with 5,000 bloggers."

In the final model, customers join for free and--based on their interests--are directed to shops curated by celebrities. Caplan said 40% of shoppers return every week.

Caplan reminded attendees that entrepreneurship and leadership are not the same things. Entrepreneurship requires "passion, vision, vigor, naive hope, and desire." Leadership, by contrast, involves "building a business that scales and is about empowering others to unlock their own potential."

The most important lesson, says Caplan: "Know how to define your own happiness."